Lithium Hydroxide → HCID 9846962, compound

HRID 2083919Notes

Reaction equation

HRID 2083919 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][C:8]=1[OH:28])C.Br.Br[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1.[H-].[Na+].[Li+].[OH-]>O1CCCC1>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:29])=[C:8]([O:28][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 10475786HCID 10475786, compound

Product 1

HCID 9846962HCID 9846962, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{2-Hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (100 mg, 0.25 mmol) and 2-bromomethylpyridine hydrobromide (70 mg, 0.28 mmol) were combined in anhydrous tetrahydrofuran (1 mL) and purged with nitrogen. Sodium hydride (60% in mineral oil, 21 mg, 0.53 mmol) was added. After stirring 24 hours, excess LiOH (1 M) was added, and stirring was continued an additional 24 hours. The reaction mixture was evaporated and chromatographed (silica gel, gradient of 5% ethyl acetate in hexanes to 2% methanol in ethyl acetate) to give 8.4 mg of the title compound. MS m/z 487 (M+H)+.

Workup

  1. custompurged with nitrogen
  2. stirringstirring
  3. waitwas continued an additional 24 hours
  4. customThe reaction mixture was evaporated
  5. customchromatographed (silica gel, gradient of 5% ethyl acetate in hexanes to 2% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-ada4099f445541eba339e35f811719a5
Source dataset
uspto-grants-2004_04
Patent number
US06716842B2

Reaction notes

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